Hydroxyamine hydrochloride → HCID 72757836, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-methoxy-phenyl)-7-(3-morpholin-4-yl-propoxy)-chromene-4-thione (222.0 mg, 0.38 mmol) in 4.0 mL of pyridine was added 80.0 mg (1.15 mmol) of hydroxylamine hydrochloride. The solution was stirred at 110° C. for 2 h. The solvent was removed under vacuum and the residue was treated with ice. The resulting slurry was filtered. The filter cake was washed with H2O purified by prep HPLC to afford 71.4 mg (35.5% yield) of desired product, I-26, as a yellow syrup (TFA salt). 1H NMR (500 MHz, DMSO-d6) δ 10.71 (s br, 1H), 9.99 (s, 1H), 7.88 (d, 2H), 7.79 (d, 1H), 7.08 (d, 2H), 7.02 (d, 1H), 6.99 (s, 1H), 6.88(dd, 1H), 4.16(t, 2H), 4.02(d, 2H), 3.84 (s, 3H), 3.67(t, 2H), 3.52(d, 2H), 3.31(t, 2H), 3.12(m, 2H), 2.17 (m, 2H) ppm. LC/MS: 411.2 (M+H), HPLC/Method A (Rt 4.03 min, 98.0% purity).

Provenance & Evidence